Imidazole → HCID 19697615, compound

HRID 863242Notes

Reaction equation

HRID 863242 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH:10]([CH2:18][OH:19])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]([Si:24]([CH3:27])([CH3:26])Cl)([CH3:23])([CH3:22])[CH3:21].N1C=CN=C1>C(Cl)Cl>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH:10]([CH2:18][O:19][Si:24]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:27])[CH3:26])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 19697838HCID 19697838, compound

Product 1

HCID 19697615HCID 19697615, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

11.6 g of 1-benzyl-3(R,S)-hydroxymethyl-1,2,3,4-tetrahydroquinoline (Example 29e), 8.54 g of tert-butyldimethylchlorosilane and 4.05 g of imidazole are stirred in 120 ml of methylene chloride at room temperature for 20 h. The precipitate is then filtered off and the crude product obtained after concentration of the filtrate is purified over 900 g of silica gel (mobile phase Z). 16 g of the title compound are obtained as a yellowish oil: Rf (Z)=0.66.

Workup

  1. filtrationThe precipitate is then filtered off
  2. customthe crude product obtained after concentration of the filtrate
  3. customis purified over 900 g of silica gel (mobile phase Z)

Sources & evidence

ORD record
ord-a8833fc0410f4323811098621e916fd6
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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